2-Chloroethanol → HCID 14881362, compound

HRID 1904336Notes

Reaction equation

HRID 1904336 reaction equation
[CH2:1](Cl)[CH2:2][OH:3].[OH:5][C:6]1[C:15]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:14][C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:7]=1>[OH-].[Na+].C(O)(C)(C)C>[OH:3][CH2:2][CH2:1][N:7]1[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[N:14]=[C:15]([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:6]1=[O:5]

Participants

5

Reactant 2

HCID 342-ChloroethanolHCID 178517341HCID 178517341, compound

Product 1

HCID 14881362HCID 14881362, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

Ethylene chlorohydrin (9.0 g) was added to a solution of 2-hydroxy-3-(2-phenylethyl)-5,6,7,8-tetrahydro quinoxaline (5.59 g, 22 mM) in aqueous 5N NaOH and t-butanol (60 ml), and stirred at 60° C. for 3 hours. The t-butanol was distilled off in vacuo, water was added to the residue, and the mixture was extracted three times with chloroform. The extract was dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was charged on a column of silica-gel (C-200, 170 g) packed with chloroform, and eluted with chloroform-methanol (200:1) to obtain compound 645 (6.73 g, yield: 90.9%).

Workup

  1. distillationThe t-butanol was distilled off in vacuo, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted three times with chloroform
  4. dry with materialThe extract was dried with anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe residue was charged on a column of silica-gel (C-200, 170 g)
  7. washeluted with chloroform-methanol (200:1)

Sources & evidence

ORD record
ord-c66b64e2f2654f25b89e8248862a7e0c
Source dataset
uspto-grants-1989_06
Patent number
US04837319

Reaction notes

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